Simsbury, Connecticut | Could You Live Here?

Built in 1914, Heublein Tower stands jauntily atop Connecticut’s Talcott Mountain like a ruby-tipped white feather in the cap of a town with much to celebrate. But this 165-foot landmark straight out of fairy-tale Bavaria isn’t merely decorative—it’s a destination. When autumn colors start to pop, vista-seekers make the mile-and-a-quarter trek up the Tower Trail and climb a six-story staircase to reach the tower’s observation room. Face north, and you might make out New Hampshire’s Mount Monadnock. To the east, nearby Hartford appears surprisingly Emerald City–ish. And to the west is southern Vermont. No, wait, that’s Simsbury: a suburban town of 23,000 camouflaged by farms and wild spaces, whose supercharged civic spirit will fuel six months of 350th anniversary festivities next year.

In your push to reach the top of the tower, you might have overlooked a certain blue leather chair that happens to be where Eisenhower was sitting in 1950 when he caved in to pressure to run for president. Places with hidden histories are par for the course in Simsbury, where residents are used to playing, dining, shopping, and even ordering a Starbucks soy latte inside such structures. They bike alongside Ensign-Bickford’s 19th-century fuse factories and drive past tobacco barns where Martin Luther King Jr. toiled for two formative teenage summers. The main drag, Hopmeadow Street, is a 3-D textbook of three-plus centuries of architecture, preserved yet utilized.

Here, in Connecticut’s first town to be nationally recognized as a “silver”-level bicycle-friendly community, you’ll instantly notice cyclists on five completed miles of the East Coast Greenway multiuse trail. Bike racks are ubiquitous, and the nonprofit Simsbury Free Bike makes loaners available at convenient locations.

The big steel bicycle near the town’s southern entrance was welded by local artist Vicente Garcia, whose self-built studio in the woods is itself a masterpiece. Visit it by appointment, and you’ll see Garcia’s distinctive smoke-fired ceramic vessels, which gained fame through a viral video that has sparked commissions from as far away as California. For a creator whose inspiration springs from within, Simsbury is an ideal place to be visible and to “get lost,” Garcia says. “I love to fish. I can be in the river with my little boat in 15 minutes—I’ve timed myself.”

The Setting

Surrounded by traprock ridges, with the Farmington River rippling through downtown, Simsbury exists in a not-really-on-the-way-to-anywhere bubble. No highway signs point visitors here from interstates, even though Bradley International Airport lies only 10 miles away. There’s open space to roam, as nearly one-third of the land is protected from development. Simsbury Farms, a former apple orchard transformed into a recreational hub, has public golf, tennis, swimming, and ice-skating facilities. And while construction of a riverfront park has forced the temporary closure of the Old Drake Hill Flower Bridge, the park will debut and the cherished attraction will bloom anew in time for next spring’s 350th anniversary kickoff.

Eating Out

Mornings can be sinful at Harvest Café and Bakery, where waffles are crowned with mountains of whipped cream, and Benedicts swim in Hollandaise. Indulge more healthfully with Popover Bistro & Bakery’s vegan treats or ultra-light namesake pastries, which have only 110 calories (until you add meat- or veggie-loaded scrambled eggs). Grabbing a maple-walnut scone at Ana’s Kitchen works, too.

Three chefs with the chops to cook anywhere helm restaurants in evocative old buildings here. Christopher Prosperi, who has elevated tastes in Connecticut through his classes and media appearances, recently moved his 20-year-old Metro Bis to the 1906 Ensign House, where his eclectic-American take on the fall harvest will tempt you right off the bike path. Meanwhile, Top Chef and frequent James Beard Award contender Tyler Anderson runs his “baby,” Millwright’s, in a 1680 sawmill, whose waterfall and foliage views pair with New England cuisine crafted to mimic nature’s artistry.

Finally, Simsbury native Jeffrey Lizotte offers pure culinary theater in his one-room Present Company, located in the stable of the 1868 Tariffville Mill. As they savor foraged mushrooms, squash, shellfish, and other prime fall foods, diners can take in all the action in the open kitchen. Lizotte, whose talents first emerged in Simsbury High’s culinary program and led him to stints in New York City and France, says it’s “a dream come true” to create not just meals but also new memories in the town where he grew up.

Shopping

Hopmeadow Street’s prettiest showrooms are clustered in Simsbury Town Shops. Pop in on goldsmith Sarah Byrnes and ask to see gold and silver pendants cast from her hand-carved homage to Simsbury’s Pinchot Sycamore, Connecticut’s largest tree. At the Silver Dahlia, discover decor and gifts in the forever-summer colors of brands like Vineyard Vines, as well as souvenirs that literally say Connecticut. At Ava Grace, a softer palette permeates the curated fashions, home accents, and keepsakes. Continue north to find Necker’s Toyland, a family-owned store founded in 1948 that survives on the quality and diversity of its new-fangled and nostalgic playthings.

Family Fun

Written in letters eight feet high, the word EGGS appears on a barn at Flamig Farm, but it’s spelled backward—which makes it art, not advertising, and thus avoids running afoul of the zoning board. This is the kind of creative spirit that helps keep agricultural enterprises thriving in Simsbury: Rosedale Farms has added wine tastings and a corn maze to its enticements; 250-year-old Tulmeadow Farm’s ice cream, in flavors like pumpkin and Indian pudding, can’t be beat.

Though Nevin Christensen’s family has owned Flamig Farm since 1907, “so many people think of this as their farm,” he says. Parents and kids love free-ranging around the petting zoo, cups of feed in hand for befriending barnyard beasts. By day, the scariest encounter might be a sideways glance from a beady-eyed emu, but on four October nights, hayrides through dark woods filled with live-action Halloween horrors call to brave souls ages 8 and up.

Don’t-Miss Events

Even when it’s not a big birthday year, Simsbury celebrates incessantly. Fall traditions include the historic local airport’s Fly-In, Car Show & Food Truck Festival (September 22); Tower Toot, which coaxes hikers up Talcott Mountain with German tunes and the aroma of grilled bratwurst (October 19–20); and the Spooktacular Chili Challenge (October 20). The year’s most beloved event, always held the Saturday after Thanksgiving, is a hometown holiday fest known simply as Simsbury Celebrates. Be there for the lighted fire truck parade, fireworks, and merriment in the streets, and you’ll feel uplifted by a community that counts its blessings in spades.

Uniquely Simsbury

Making this a town that’s walkable, bikeable, and fit for lovers of literature, the Storytellers’ Cottage is a one-of-a-kind enterprise situated in a mint-green Victorian mansion. It offers mystery rooms for solving, immersive events for fans of all literary genres, and open hours for reading or writing in themed spaces such as the steampunk library. A “writer in residence” is available to offer critiques of patrons’ work.

Where to Stay

Two miles and more than 150 years may separate the Simsbury Inn and Simsbury 1820 House, but guests of these sister properties share equally in access to the inn’s conservatory-style indoor pool, four dining options, and complimentary breakfasts, bikes, and shuttle transportation. Whether you choose the inn for its Talcott Mountain views or the 1820 House for its town-center convenience (or its ties to famous locals, including pioneering forester and Pennsylvania governor Gifford Pinchot), you’ll find a surprise on your pillow: a tiny historical-fiction storybook set in Simsbury.

If You Could Live Here

Most family homes in Simsbury—such as a walk-to-town, four-bedroom colonial—get snapped up when they’re priced under $300,000. Look to West Simsbury for custom-built properties like a window-walled, midcentury-modern stunner priced at $545,000. There’s new construction, too, for the first time in decades. Cambridge Crossing’s single-family homes appeal to first-time buyers and down-sizers reluctant to retire elsewhere. Got $475,000 to invest? In time-forgotten Tariffville, a 1900 Catholic church begs for divinely inspired redevelopment. 

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